Literature DB >> 25442314

Synthesis and in vitro stability of amino acid prodrugs of 6-β-naltrexol for microneedle-enhanced transdermal delivery.

Joshua A Eldridge1, Mikolaj Milewski2, Audra L Stinchcomb3, Peter A Crooks4.   

Abstract

A small library of amino acid ester prodrugs of 6-β-naltrexol (NTXOL, 1) was prepared in order to investigate the candidacy of these prodrugs for microneedle-enhanced transdermal delivery. Six amino acid ester prodrugs were synthesized (6a-f). 6b, 6d, and 6 e were stable enough at skin pH (pH 5.0) to move forward to studies in 50% human plasma. The lead compound (6 e) exhibited the most rapid bioconversion to NTXOL in human plasma (t1/2 = 2.2 ± 0.1h).
Copyright © 2014 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Amino acid esters; Microneedles; Prodrugs; Stability; Transdermal

Mesh：

Substances：

Year:  2014        PMID： 25442314      PMCID： PMC4254627          DOI： 10.1016/j.bmcl.2014.09.072

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  23 in total

1.  Enhancement of transdermal delivery of 6-beta-naltrexol via a codrug linked to hydroxybupropion.

Authors:  Paul K Kiptoo; Mohamed O Hamad; Peter A Crooks; Audra L Stinchcomb
Journal:  J Control Release       Date:  2006-04-25       Impact factor: 9.776

2.  Synthesis and hydrolytic behavior of two novel tripartate codrugs of naltrexone and 6beta-naltrexol with hydroxybupropion as potential alcohol abuse and smoking cessation agents.

Authors:  Mohamed O Hamad; Paul K Kiptoo; Audra L Stinchcomb; Peter A Crooks
Journal:  Bioorg Med Chem       Date:  2006-06-23       Impact factor: 3.641

Review 3.  Micro-scale devices for transdermal drug delivery.

Authors:  Anubhav Arora; Mark R Prausnitz; Samir Mitragotri
Journal:  Int J Pharm       Date:  2008-08-30       Impact factor: 5.875

4.  In vitro permeation of a pegylated naltrexone prodrug across microneedle-treated skin.

Authors:  Mikolaj Milewski; Thirupathi Reddy Yerramreddy; Priyanka Ghosh; Peter A Crooks; Audra L Stinchcomb
Journal:  J Control Release       Date:  2010-06-04       Impact factor: 9.776

Review 5.  Current aspects of formulation efforts and pore lifetime related to microneedle treatment of skin.

Authors:  Mikolaj Milewski; Nicole K Brogden; Audra L Stinchcomb
Journal:  Expert Opin Drug Deliv       Date:  2010-05       Impact factor: 6.648

6.  A duplex "Gemini" prodrug of naltrexone for transdermal delivery.

Authors:  Dana C Hammell; Mohamed Hamad; Haranath K Vaddi; Peter A Crooks; Audra L Stinchcomb
Journal:  J Control Release       Date:  2004-06-18       Impact factor: 9.776

7.  Flux across [corrected] microneedle-treated skin is increased by increasing charge of naltrexone and naltrexol in vitro.

Authors:  Stan L Banks; Raghotham R Pinninti; Harvinder S Gill; Peter A Crooks; Mark R Prausnitz; Audra L Stinchcomb
Journal:  Pharm Res       Date:  2008-05-01       Impact factor: 4.200

8.  In vivo evaluation of a transdermal codrug of 6-beta-naltrexol linked to hydroxybupropion in hairless guinea pigs.

Authors:  Paul K Kiptoo; Kalpana S Paudel; Dana C Hammell; Mohamed O Hamad; Peter A Crooks; Audra L Stinchcomb
Journal:  Eur J Pharm Sci       Date:  2008-01-31       Impact factor: 4.384

9.  Microneedles permit transdermal delivery of a skin-impermeant medication to humans.

Authors:  Daniel P Wermeling; Stan L Banks; David A Hudson; Harvinder S Gill; Jyoti Gupta; Mark R Prausnitz; Audra L Stinchcomb
Journal:  Proc Natl Acad Sci U S A       Date:  2008-02-04       Impact factor: 11.205

10.  Transdermal delivery of naltrexol and skin permeability lifetime after microneedle treatment in hairless guinea pigs.

Authors:  Stan L Banks; Raghotham R Pinninti; Harvinder S Gill; Kalpana S Paudel; Peter A Crooks; Nicole K Brogden; Mark R Prausnitz; Audra L Stinchcomb
Journal:  J Pharm Sci       Date:  2010-07       Impact factor: 3.534
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  2 in total

1.  Small cyclic agonists of iron regulatory hormone hepcidin.

Authors:  Kristine Chua; Eileen Fung; Ewa D Micewicz; Tomas Ganz; Elizabeta Nemeth; Piotr Ruchala
Journal:  Bioorg Med Chem Lett       Date:  2015-03-12       Impact factor: 2.823

2.  Small lipidated anti-obesity compounds derived from neuromedin U.

Authors:  Ewa D Micewicz; Omar S O Bahattab; Gary B Willars; Alan J Waring; Mohamad Navab; Julian P Whitelegge; William H McBride; Piotr Ruchala
Journal:  Eur J Med Chem       Date:  2015-07-14       Impact factor: 6.514
  2 in total

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